The Obstacle is the Way Summary

Ryan Holiday is one of those people you read about and can’t help but admire. He dropped out of college to work with Robert Greene and has advised some extremely successful authors including Tim Ferriss and Tucker Max. He also served as the director of marketing for American Apparel. He owes much of his success to the ideas and lessons he learned from stoicism.

This brings us back to The Obstacle is the Way, which is the first book on stoicism I’ve ever read, and it’s an absolute gem. You may be asking yourself “What does stoicism have to do with art?”, but that is the wrong question. The real question is “How does stoicism help me in life?” First, let’s explore what stoicism is.

Stoicism is a systematic philosophy, dating from around 300 b.c., that held the principles of logical thought to reflect a cosmic reason instantiated in nature.

What this means in plain terms is stoicism forces you to look at every situation logically. Instead of letting your emotions take over your decision making, you must look at every situation objectively to find a logical solution. This may seem hard for artists, who are normally very passionate people, but I have found removing your emotions from a problem makes the solution much clearer.

Will: In the final section, Ryan explores having discipline, anticipating the worst, perseverance, and being ready to start over. Perception and action will only get you so far, if your will is broken. Knowing how everything is connected and acknowledging things happen for a reason is the glue that holds you together.

This book has an incredible number of great examples to back up each point. Without great stories to back it up, philosophy is just someone’s theory. Luckily, Holiday explores how some of the most influential people in history who have used and adopted stoic principles. He provides examples ranging from Roman emperor Marcus Aurelius to US President Barack Obama, and many people in-between. If you are interested in reading these stories, I highly recommend picking up this book.

“See things for what they are. Do what we can. Endure and bear what we must. What blocked the path now is a path. What once impeded action advances action. The Obstacle is the Way.” – Ryan Holiday

Kindle Highlights for The Obstacle is the Way

(LOCATIONS are for Kindle)

The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph
Ryan Holiday

Our actions may be impeded . . . but there can be no impeding our intentions or dispositions. Because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting.
LOCATION: 87

The impediment to action advances action. What stands in the way becomes the way.
LOCATION: 90

turning obstacles upside down.
LOCATION: 92

what impedes us can empower us.
LOCATION: 94

he truly saw each and every one of these obstacles as an opportunity to practice some virtue: patience, courage, humility, resourcefulness, reason, justice, and creativity.
LOCATION: 98

he proved himself worthy of it.
LOCATION: 101

We might not be emperors, but the world is still constantly testing us.
LOCATION: 114

Objective judgment, now at this very moment. Unselfish action, now at this very moment. Willing acceptance—now at this very moment—of all external events. That’s all you need. —MARCUS AURELIUS
LOCATION: 223

Perception, Action, and the Will.
LOCATION: 229

WHAT IS PERCEPTION? It’s how we see and understand what occurs around us—and what we decide those events will mean.
LOCATION: 238

The market was inherently unpredictable and often vicious—only the rational and disciplined mind could hope to profit from it.
LOCATION: 258

He was inclined to see the opportunity in every disaster.
LOCATION: 266

the greater the chaos, the calmer Rockefeller would become,
LOCATION: 269

Warren Buffet’s famous adage to “be fearful when others are greedy and greedy when others are fearful.”
LOCATION: 271

You will come across obstacles in life—fair and unfair. And you will discover, time and time again, that what matters most is not what these obstacles are but how we see them, how we react to them, and whether we keep our composure. You will learn that this reaction determines how successful we will be in overcoming—or possibly thriving because of—them.
LOCATION: 284

Nothing makes us feel this way; we choose to give in to such feelings.
LOCATION: 289

To be objective To control emotions and keep an even keel To choose to see the good in a situation To steady our nerves To ignore what disturbs or limits others To place things in perspective To revert to the present moment To focus on what can be controlled
LOCATION: 314

The perceiving eye is weak, he wrote; the observing eye is strong.
LOCATION: 487

the next time someone intimidates you or makes you feel insecure. See them in your mind, grunting, groaning, and awkward in their private life—just like the rest of us.
LOCATION: 506

The aim was to see these things as they really are, without any of the ornamentation.
LOCATION: 509

Something that’s present when we deal with our own obstacles is always missing when we hear other people’s problems: the baggage. With other people we can be objective.
LOCATION: 514

The more skilled you become seeing things for what they are, the more perception will work for you rather than against you.
LOCATION: 521

Man does not simply exist but always decides what his existence will be, what he will become the next moment. By the same token, every human being has the freedom to change at any instant. —VIKTOR FRANKL
LOCATION: 523

Perspective is everything.
LOCATION: 532

Fear is debilitating, distracting, tiring, and often irrational.
LOCATION: 533

The task, as Pericles showed, is not to ignore fear but to explain it away. Take what you’re afraid of—when fear strikes you—and break it apart.
LOCATION: 536

How we approach, view, and contextualize an obstacle, and what we tell ourselves it means, determines how daunting and trying it will be to overcome.
LOCATION: 539

When it comes to perception, this is the crucial distinction to make: the difference between the things that are in our power and the things that aren’t.
LOCATION: 622

Focusing exclusively on what is in our power magnifies and enhances our power.
LOCATION: 627

The trick to forgetting the big picture is to look at everything close up. —CHUCK PALAHNIUK
LOCATION: 633

this moment is not your life, it’s just a moment in your life.
LOCATION: 676

Genius is the ability to put into effect what is in your mind. There’s no other definition of it. —F. SCOTT FITZGERALD
LOCATION: 680

This was Jobs’s view of reality at work. Malleable, adamant, self-confident.
LOCATION: 690

He knew that to aim low meant to accept mediocre accomplishment. But a high aim could, if things went right, create something extraordinary.
LOCATION: 691

Our perceptions determine, to an incredibly large degree, what we are and are not capable of.
LOCATION: 696

This is why we shouldn’t listen too closely to what other people say
LOCATION: 700

We’ll find ourselves erring on the side of accomplishing nothing.
LOCATION: 701

An entrepreneur is someone with faith in their ability to make something where there was nothing before.
LOCATION: 722

A good person dyes events with his own color . . . and turns whatever happens to his own benefit. —SENECA
LOCATION: 728

As Laura Ingalls Wilder put it: “There is good in everything, if only we look for it.”
LOCATION: 754

every situation is an opportunity for us to act.
LOCATION: 759

The extent of the struggle determines the extent of the growth.
LOCATION: 786

Action is commonplace, right action is not.
LOCATION: 821

We must be sure to act with deliberation, boldness, and persistence.
LOCATION: 824

Some academic once asked Demosthenes what the three most important traits of speechmaking were. His reply says it all: “Action, Action, Action!”
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You’ve got to act. And you’ve got to start now.
LOCATION: 872

It matters what you do with what happens and what you’ve been given.
LOCATION: 873

Because each obstacle we overcome makes us stronger for the next one.
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Therefore, we can always (and only) greet our obstacles with energy with persistence with a coherent and deliberate process with iteration and resilience with pragmatism with strategic vision with craftiness and savvy and an eye for opportunity and pivotal moments
LOCATION: 890

We must all either wear out or rust out, every one of us. My choice is to wear out. —THEODORE ROOSEVELT
LOCATION: 897

Because they know that once they get started, if they can just get some momentum, they can make it work.
LOCATION: 907

“Always think with your stick forward.”
LOCATION: 938

Be deliberate, of course, but you always need to be moving forward. And that’s the final part: Stay moving, always.
LOCATION: 938

He says the best way out is always through And I agree to that, or in so far As I can see no way out but through. —ROBERT FROST
LOCATION: 956

We will not be stopped by failure, we will not be rushed or distracted by external noise.
LOCATION: 972

in exhausting all the other traditional options, he’d been forced to try something new.
LOCATION: 974

Stop looking for an epiphany, and start looking for weak points.
LOCATION: 1020

What is defeat? Nothing but education; nothing but the first steps to something better. —WENDELL PHILLIPS
LOCATION: 1025

Failure really can be an asset if what you’re trying to do is improve, learn, or do something new.
LOCATION: 1031

great success are often preceded by epic failure—because
LOCATION: 1046

Great entrepreneurs are: never wedded to a position never afraid to lose a little of their investment never bitter or embarrassed never out of the game for long
LOCATION: 1051

Thickheaded and resistant to change, these are the types who are too self-absorbed to realize that the world doesn’t have time to plead, argue, and convince them of their errors.
LOCATION: 1071

Lessons come hard only if you’re deaf to them.
LOCATION: 1075

Under the comb the tangle and the straight path are the same. —HERACLITUS
LOCATION: 1079

That’s the process: Let’s think about what we can do today, the task at hand.”
LOCATION: 1088

something very difficult.
LOCATION: 1090

break it down into pieces.
LOCATION: 1090

do what you need to do right now. And do it well. And then move on to the next thing.
LOCATION: 1090

Excellence is a matter of steps.
LOCATION: 1092

not getting distracted
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The process is about finishing.
LOCATION: 1094

Don’t think about the end—think about surviving.
LOCATION: 1097

When it comes to our actions, disorder and distraction are death.
LOCATION: 1113

Being trapped is just a position, not a fate.
LOCATION: 1124

When we know what we’re really setting out to do, the obstacles that arise tend to seem smaller, more manageable. When we don’t, each one looms larger and seems impossible.
LOCATION: 1134

The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture.
LOCATION: 1144

Everything is a chance to do and be your best.
LOCATION: 1166

When action is our priority, vanity falls away.
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if we do our best we can be proud of our choices and confident they’re the right ones.
LOCATION: 1180

But duty is beautiful, and inspiring and empowering.
LOCATION: 1182

all we need to do is those three little duties—to try hard, to be honest, and to help others and ourselves.
LOCATION: 1194

Forget the rule book, settle the issue.
LOCATION: 1212

Pragmatism is not so much realism as flexibility.
LOCATION: 1240

Start thinking like a radical pragmatist: still ambitious, aggressive, and rooted in ideals, but also imminently practical and guided by the possible.
LOCATION: 1248

Think progress, not perfection.
LOCATION: 1251

As Hart writes in his masterwork Strategy: [T]he Great Captain will take even the most hazardous indirect approach—if necessary over mountains, deserts or swamps, with only a fraction of the forces, even cutting himself loose from his communications. Facing, in fact, every unfavorable condition rather than accept the risk of stalemate invited by direct approach.
LOCATION: 1278

exert only calculated force where it will be effective, rather than straining and struggling with pointless attrition tactics.
LOCATION: 1293

You don’t convince people by challenging their longest and most firmly held opinions. You find common ground and work from there.
LOCATION: 1311

Wise men are able to make a fitting use even of their enmities. —PLUTARCH
LOCATION: 1320

Sometimes you overcome obstacles not by attacking them but by withdrawing and letting them attack you.
LOCATION: 1325

Opposites work. Nonaction can be action.
LOCATION: 1333

So instead of fighting obstacles, find a means of making them defeat themselves.
LOCATION: 1344

Passive resistance is, in fact, incredibly active. But those actions come in the form of discipline, self-control, fearlessness, determination, and grand strategy.
LOCATION: 1368

When jarred, unavoidably, by circumstance revert at once to yourself and don’t lose the rhythm more than you can help. You’ll have a better grasp of harmony if you keep going back to it. —MARCUS AURELIUS
LOCATION: 1380

But physical looseness combined with mental restraint? That is powerful.
LOCATION: 1416

The best men are not those who have waited for chances but who have taken them; besieged chance, conquered the chance, and made chance the servitor. —E. H. CHAPIN
LOCATION: 1420

paralyzed by fear that they defer taking action.
LOCATION: 1426

Their typical response is to hide, ignore, obfuscate, or distance themselves.
LOCATION: 1427

neutralized a potentially fatal controversy but created an opportunity to seize the electoral high ground.
LOCATION: 1432

learn how to press forward precisely when everyone around you sees disaster.
LOCATION: 1436

act swiftly and unexpectedly to pull off a big victory. While others are arrested by discouragement, we are not.
LOCATION: 1437

“You never want a serious crisis to go to waste. Things that we had postponed for too long, that were long-term, are now immediate and must be dealt with. [A] crisis provides the opportunity for us to do things that you could not do before.”
LOCATION: 1439

Seize this moment to deploy the plan that has long sat dormant in your head.
LOCATION: 1447

Napoleon described war in simple terms: Two armies are two bodies that clash and attempt to frighten each other. At impact, there is a moment of panic and it is that moment that the superior commander turns to his advantage.
LOCATION: 1457

It’s the one who rises the next morning after a long day of fighting and rallies,
LOCATION: 1467

now—who will carry victory home . . . intelligently.
LOCATION: 1468

Nothing can ever prevent us from trying. Ever.
LOCATION: 1479

some obstacles may turn out to be impossible to overcome.
LOCATION: 1480

turn that obstacle upside down, too, simply by using it as an opportunity to practice some other virtue or skill—even
LOCATION: 1482

In every situation, that which blocks our path actually presents a new path with a new part of us.
LOCATION: 1484

Sometimes, no amount of planning, no amount of thinking—no matter how hard we try or patiently we persist—will change the fact that some things just aren’t going to work.
LOCATION: 1489

Will is our internal power, which can never be affected by the outside world.
LOCATION: 1494

Placed in some situation that seems unchangeable and undeniably negative, we can turn it into a learning experience, a humbling experience, a chance to provide comfort to others. That’s will power.
LOCATION: 1496

In actuality, the will has a lot more to do with surrender than with strength.
LOCATION: 1499

True will is quiet humility, resilience, and flexibility; the other kind of will is weakness disguised by bluster and ambition.
LOCATION: 1501

“In every generation a person is obligated to view himself as if he were the one who went out of Egypt.”
LOCATION: 1615

it prompts those partaking in the feast to visualize and possess the strength that has kept them going.
LOCATION: 1617

Inner Citadel, that fortress inside of us that no external adversity can ever break down.
LOCATION: 1619

we are not born with such a structure; it must be built and actively reinforced.
LOCATION: 1620

we should always prepare for things to get tough.
LOCATION: 1625

If we’re going to succeed in achieving our goals despite the obstacles that may come, this strength in will must be built.
LOCATION: 1627

The path of least resistance is a terrible teacher. We can’t afford to shy away from the things that intimidate us.
LOCATION: 1632

A premortem is different. In it, we look to envision what could go wrong, what will go wrong, in advance, before we start.
LOCATION: 1649

Far too many people don’t have a backup plan because they refuse to consider that something might not go exactly as they wish.
LOCATION: 1650

“Nothing happens to the wise man against his expectation,” he wrote to a friend. “. . . nor do all things turn out for him as he wished but as he reckoned—and above all he reckoned that something could block his plans.”
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sometimes the only answer to “What if . . .” is, It will suck but we’ll be okay.
LOCATION: 1671

The only guarantee, ever, is that things will go wrong.
LOCATION: 1678

It’s far better to seem like a downer than to be blindsided or caught off guard.
LOCATION: 1683

the person who has rehearsed in their mind what could go wrong will not be caught by surprise.
LOCATION: 1694

With anticipation, we can endure. We are prepared for failure and ready for success.
LOCATION: 1701

The Fates guide the person who accepts them and hinder the person who resists them. —CLEANTHES
LOCATION: 1703

It doesn’t always feel that way but constraints in life are a good thing.
LOCATION: 1714

They push us to places and to develop skills that we’d otherwise never have pursued.
LOCATION: 1715

“True genius,” as the infamous Dr. Samuel Johnson once said, “is a mind of large general powers accidentally determined in some particular direction.”
LOCATION: 1716

When the cause of our problem lies outside of us, we are better for accepting it and moving on.
LOCATION: 1731

We instinctively think about how much better we’d like any given situation to be.
LOCATION: 1743

We still can’t appreciate what we have.
LOCATION: 1749

Follow where the events take you, like water rolling down a hill—it always gets to the bottom
LOCATION: 1768

As Francis Bacon once said, nature, in order to be commanded, must be obeyed.
LOCATION: 1772

My formula for greatness in a human being is amor fati: that one wants nothing to be different, not forward, not backward, not in all eternity. Not merely bear what is necessary, still less conceal it . . . but love it. —NIETZSCHE
LOCATION: 1774

To do great things, we need to be able to endure tragedy and setbacks.
LOCATION: 1788

We have to learn to find joy in every single thing that happens.
LOCATION: 1789

loving whatever happens to us and facing it with unfailing cheerfulness.
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It is the act of turning what we must do into what we get to do.
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In your worst moments, picture Johnson: always calm, always in control, genuinely loving the opportunity to prove himself, to perform for people, whether they wanted him to succeed or not.
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more—letting the opponent dig his own grave.
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Cheerfulness in all situations, especially the bad ones.
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We don’t get to choose what happens to us, but we can always choose how we feel about it.
LOCATION: 1829

And you don’t just want fuel. You need it.
LOCATION: 1837

Persistence. Everything directed at one problem, until it breaks.
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If persistence is attempting to solve some difficult problem with dogged determination and hammering until the break occurs, then plenty of people can be said to be persistent. But perseverance is something larger. It’s the long game.
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round two and every round after—and then the fight after that and the fight after that, until the end.
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Life is not about one obstacle, but many.
LOCATION: 1860

a determination that we will get to where we need to go, somehow, someway, and nothing will stop us.
LOCATION: 1861

Persistence is an action. Perseverance is a matter of will.
LOCATION: 1863

This is perseverance. And with it, Emerson said, “with the exercise of self-trust, new powers shall appear.”
LOCATION: 1889

Beethoven: “The barriers are not erected which can say to aspiring talents and industry, Thus far and no farther.”
LOCATION: 1890

Determination, if you think about it, is invincible.
LOCATION: 1895

We don’t control the barriers or the people who put them there. But we control ourselves—and that is sufficient.
LOCATION: 1898

The true threat to determination, then, is not what happens to us, but us ourselves.
LOCATION: 1899

We’re in this together, he told them. He gave them a watchword to remind them: U.S.—Unity over Self.
LOCATION: 1922

But their cause was their men. They cared about their fellow prisoners and drew great strength by putting their well-being ahead of their own.
LOCATION: 1927

when we focus on others, on helping them or simply providing a good example, our own personal fears and troubles will diminish.
LOCATION: 1938

Shared purpose gives us strength.
LOCATION: 1940

one of the best ways to create opportunities or new avenues for movement is to think: If I can’t solve this for myself, how can I at least make this better for other people?
LOCATION: 1943

If not for me, then for my family or the others I’m leading or those who might later find themselves in a similar situation.
LOCATION: 1946

They figure out what they need to do and do it, fitting in as much as possible before the clock expires.
LOCATION: 2015

if even our own mortality can have some benefit, how dare you say that you can’t derive value from each and every other kind of obstacle you encounter?
LOCATION: 2023

The great law of nature is that it never stops. There is no end. Just when you think you’ve successfully navigated one obstacle, another emerges.
LOCATION: 2028

But that’s what keeps life interesting.
LOCATION: 2029

that’s what creates opportunities.
LOCATION: 2029

Each time, you’ll learn something. Each time, you’ll develop strength, wisdom, and perspective. Each time, a little more of the competition falls away. Until all that is left is you: the best version of you.
LOCATION: 2031

Elysium is a myth. One does not overcome an obstacle to enter the land of no obstacles.
LOCATION: 2033

the more you accomplish, the more things will stand in your way.
LOCATION: 2034

Knowing that life is a marathon and not a sprint is important. Conserve your energy.
LOCATION: 2036

Never rattled. Never frantic. Always hustling and acting with creativity.
LOCATION: 2040

Simply flipping the obstacles that life throws at you by improving in spite of them, because of them.
LOCATION: 2041

They would capture Cassius and endeavor not to kill him, but “. . . forgive a man who has wronged one, to remain a friend to one who has transgressed friendship, to continue faithful to one who has broken faith.”
LOCATION: 2052

“settle this affair well and show to all mankind that there is a right way to deal even with civil wars.”
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Marcus refused to put any coconspirators to death. He declined to prosecute any of the senators or governors who had endorsed or expressed support for the uprising.
LOCATION: 2067

“I implore you, the senate, to keep my reign unstained by the blood of any senator. May it never happen.”
LOCATION: 2069

Something stands in someone’s way. They stare it down, they aren’t intimidated. Leaning into their problem or weakness or issue, they give everything they have, mentally and physically. Even though they did not always overcome it in the way they intended or expected, each individual emerged better, stronger.
LOCATION: 2077

We can see the “bad” things that happen in our lives with gratitude and not with regret because we turn them from disaster to real benefit—from
LOCATION: 2085

First, see clearly. Next, act correctly. Finally, endure and accept the world as it is.
LOCATION: 2091

Our actions give us the confidence to ignore or control our perceptions. We prove and support our will with our actions.
LOCATION: 2094

Like Rockefeller, you’re cool under pressure, immune to insults and abuse. You see opportunity in the darkest of places.
LOCATION: 2106

Like Demosthenes, you assume responsibility for yourself—teaching yourself, compensating for disadvantages, and pursuing your rightful calling and place in the world.
LOCATION: 2107

Like Lincoln, you realize that life is a trial. It will not be easy, but you are prepared to give it everything you have regardless, ready to endure, persevere, and inspire others.
LOCATION: 2109

See things for what they are. Do what we can. Endure and bear what we must. What blocked the path now is a path. What once impeded action advances action. The Obstacle is the Way.
LOCATION: 2114

To be a philosopher is not merely to have subtle thoughts, nor even to found a school . . . it is to solve some of the problems of life, not only theoretically, but practically. —HENRY DAVID THOREAU
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